I think the problem with this angle of argument is that it pretty much solely relies on extreme empathy holding from current homeowners (aka those with power). And when that empathy is worn down, such as the example woman in the oliver segment who has to pick up human poop on a regular basis, then the argument just falls completely flat. Like it basically goes like this "Look how bad these ppl have it, don't you care?" and the answer is "No." - then what do you do? There's no avenue for follow up or iteration - you've just made a assumption just completely breaks.
You can criticize the housed-first perspectives, but at least they try to find win-win common ground between the interest of the house (not picking up human poop) and the homeless (get a home). I'm also a big fan of the tax/finance forward methods and oliver had an example during his segment of a way to save $ per homeless per year spending.
To me this article reads as the epitome of 'bleeding-heart' syndrome, and lacking critical thinking toward actual problem solving with multiple stake holder interests in play.